Regioselective Synthesis of Polyheterohalogenated Naphthalenes via the Benzannulation of Haloalkynes
作者:Dan Lehnherr、Joaquin M. Alzola、Emil B. Lobkovsky、William R. Dichtel
DOI:10.1002/chem.201503418
日期:2015.12.7
control of halide substitution at six of the seven naphthalene positions of 2‐arylnaphthalenes is achieved through the regioselective benzannulation of chloro‐, bromo‐, and iodoalkynes. The modularity of this approach is demonstrated through the preparation of 44 polyheterohalogenated naphthalene products, most of which are difficult to access through known naphthalene syntheses. The outstanding regioselectivity
通过氯,溴和碘炔的区域选择性苯环烷基化,可以实现2-芳基萘七个萘位置中六个位置上卤化物取代的独立控制。该方法的模块化通过制备44种多卤代萘产品得到了证明,其中大多数产品都难以通过已知的萘合成方法获得。对于许多实例,反应的出色区域选择性既可以预测,也可以通过单晶X射线衍射明确证明。这种合成方法能够使用已建立的交叉偶联方法快速制备准备进一步衍生化的复杂芳香族体系。